CA2876306C - Deuterated derivatives of ruxolitinib - Google Patents
Deuterated derivatives of ruxolitinib Download PDFInfo
- Publication number
- CA2876306C CA2876306C CA2876306A CA2876306A CA2876306C CA 2876306 C CA2876306 C CA 2876306C CA 2876306 A CA2876306 A CA 2876306A CA 2876306 A CA2876306 A CA 2876306A CA 2876306 C CA2876306 C CA 2876306C
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- CA
- Canada
- Prior art keywords
- compound
- salt
- deuterium
- hydrogen
- myelofibrosis
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 186
- 150000003839 salts Chemical class 0.000 claims abstract description 62
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- 229910052805 deuterium Inorganic materials 0.000 claims description 111
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 109
- 239000003814 drug Substances 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 229940124597 therapeutic agent Drugs 0.000 claims description 38
- 206010028537 myelofibrosis Diseases 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 22
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- 230000000694 effects Effects 0.000 claims description 19
- 238000010348 incorporation Methods 0.000 claims description 17
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- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 15
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- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 7
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- HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical class C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
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- 239000012317 TBTU Substances 0.000 description 6
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
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- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
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| US201261678795P | 2012-08-02 | 2012-08-02 | |
| US61/678,795 | 2012-08-02 | ||
| PCT/US2013/045919 WO2013188783A1 (en) | 2012-06-15 | 2013-06-14 | Deuterated derivatives of ruxolitinib |
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| CA2876306A1 CA2876306A1 (en) | 2013-12-19 |
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| CA2876306A Active CA2876306C (en) | 2012-06-15 | 2013-06-14 | Deuterated derivatives of ruxolitinib |
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| MY165963A (en) | 2011-06-20 | 2018-05-18 | Incyte Holdings Corp | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| LT3882249T (lt) | 2012-06-15 | 2025-08-25 | Sun Pharmaceutical Industries, Inc. | Ruksolitinibo deuterinti dariniai |
| SG10202111768XA (en) | 2012-11-15 | 2021-11-29 | Incyte Holdings Corp | Sustained-release dosage forms of ruxolitinib |
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- 2013-06-14 PT PT211563986T patent/PT3882249T/pt unknown
- 2013-06-14 DK DK18188152.5T patent/DK3450434T3/da active
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